Background
As a young Rizzling on Batuu, Skippy came up as a spice runner and enforcer for the Terrible Quenkers Cartel. As the Republic fell to the Empire, it became advantageous for the Quenkers to present themselves as a freedom fighter organization, espousing revolutionary ideals as a cover for their illicit activities. This cover worked so well that the Terrible Quenkers became accepted as a legitimate group within the Rebel Alliance.
As the Galactic Civil War progressed and Skippy advanced in age, Skippy found himself taking on more legitimate security roles within the Rebellion and now the New Republic, his criminal history providing him with a valuable knowledge base. Skippy rose through the ranks of the new Republic, eventually achieving the role of Security Chairman of the Department of Commerce of the Trilon sector. Despite this, Skippy is far from a patriot. Skippy uses his placement within the bureaucracy to enrich himself and assist his former gang-mates in their illicit commerce. Skippy has recently been greatly demoted after being implicated in the sale of many illicit goods in the Trilon sector. While unable to establish a definitive link between these sales and Skippy, New Republic prosecutors determined that at minimum, they were enabled by Skippy's incompetence, if not willful ignorance.
Motivation
Skippy is good at what he does and enjoys doing it. While he may claim to only want to support his family, and others will say he's in it for the money, Skippy is in this game for the good of the game, enjoying the thrill of narrowly avoiding detection.